γ-Butyrolactones from Aspergillus Species: Structures, Biosynthesis, and Biological Activities

Recently, numerous metabolites possessing uncommon structures and potent bioactivity have been isolated from strains of fungi collected from diverse environments. The genus Aspergillus is known as a rich source of γ-butyrolactones. These are a group of fungal secondary metabolites, consisting of a five-membered lactone bearing two aromatic rings, which shows a great variety of biological activities. This review summarizes the research on the biosynthesis, source, and biological activities of the naturally occurring γ-butyrolactones that have been isolated from Aspergillus species published over the last decades. More than 75 compounds are described and 65 references are cited.

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Natural Product Repertoire of the Genus Amphimedon

Marine Drugs ◽

10.3390/md17010019 ◽

2018 ◽

Vol 17 (1) ◽

pp. 19 ◽

Cited By ~ 5

Author(s):

Nourhan Shady ◽

Mostafa Fouad ◽

Mohamed Salah Kamel ◽

Tanja Schirmeister ◽

Usama Abdelmohsen

Keyword(s):

Secondary Metabolites ◽

Natural Product ◽

Bioactive Compounds ◽

Biological Activities ◽

Marine Sponges ◽

Rich Source ◽

Undescribed Species ◽

Pharmacological Activities ◽

Wide Range ◽

Complete Survey

Marine sponges are a very attractive and rich source in the production of novel bioactive compounds. The sponges exhibit a wide range of pharmacological activities. The genus Amphimedon consists of various species, such as viridis, compressa, complanata, and terpenensis, along with a handful of undescribed species. The Amphimedon genus is a rich source of secondary metabolites containing diverse chemical classes, including alkaloids, ceramides, cerebrososides, and terpenes, with various valuable biological activities. This review covers the literature from January 1983 until January 2018 and provides a complete survey of all the compounds isolated from the genus Amphimedon and the associated microbiota, along with their corresponding biological activities, whenever applicable.

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Bioactivities and Future Perspectives of Chaetoglobosins

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2020/8574084 ◽

2020 ◽

Vol 2020 ◽

pp. 1-10 ◽

Cited By ~ 2

Author(s):

Jinhua Chen ◽

Wenzhou Zhang ◽

Qingfeng Guo ◽

Weijiang Yu ◽

Yongna Zhang ◽

...

Keyword(s):

Secondary Metabolites ◽

Large Class ◽

Biological Activities ◽

Mechanisms Of Action ◽

Chaetomium Globosum ◽

Future Perspectives ◽

Anti Inflammatory ◽

Anti Hiv ◽

Fungal Secondary Metabolites

Chaetoglobosins belonging to cytochalasan alkaloids represent a large class of fungal secondary metabolites. To date, around 100 chaetoglobosins and their analogues have been isolated and identified over the years from a variety of fungi, mainly from the fungus Chaetomium globosum. Studies have found that chaetoglobosins possess a broad range of biological activities, including antitumor, antifungal, phytotoxic, fibrinolytic, antibacterial, nematicidal, anti-inflammatory, and anti-HIV activities. This review will comprehensively summarize the biological activities and mechanisms of action of nature-derived chaetoglobosins.

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Chromatin-dependent regulation of secondary metabolite biosynthesis in fungi: is the picture complete?

FEMS Microbiology Reviews ◽

10.1093/femsre/fuz018 ◽

2019 ◽

Cited By ~ 4

Author(s):

Jérôme Collemare ◽

Michael F Seidl

Keyword(s):

Secondary Metabolites ◽

Secondary Metabolite ◽

Biological Activities ◽

Gene Clusters ◽

Research Field ◽

Chromatin Modifications ◽

Biosynthetic Gene ◽

Biosynthetic Gene Clusters ◽

Post Translational Modifications ◽

Fungal Secondary Metabolites

ABSTRACTFungal secondary metabolites are small molecules that exhibit diverse biological activities exploited in medicine, industry and agriculture. Their biosynthesis is governed by co-expressed genes that often co-localize in gene clusters. Most of these secondary metabolite gene clusters are inactive under laboratory conditions, which is due to a tight transcriptional regulation. Modifications of chromatin, the complex of DNA and histone proteins influencing DNA accessibility, play an important role in this regulation. However, tinkering with well-characterised chemical and genetic modifications that affect chromatin alters the expression of only few biosynthetic gene clusters, and thus the regulation of the vast majority of biosynthetic pathways remains enigmatic. In the past, attempts to activate silent gene clusters in fungi mainly focused on histone acetylation and methylation, while in other eukaryotes many other post-translational modifications are involved in transcription regulation. Thus, how chromatin regulates the expression of gene clusters remains a largely unexplored research field. In this review, we argue that focusing on only few well-characterised chromatin modifications is significantly hampering our understanding of the chromatin-based regulation of biosynthetic gene clusters. Research on underexplored chromatin modifications and on the interplay between different modifications is timely to fully explore the largely untapped reservoir of fungal secondary metabolites.

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BIOLOGICAL ACTIVITIES AND NOVEL APPLICATIONS OF CHALCONES

Planta Daninha ◽

10.1590/s0100-83582016340300022 ◽

2016 ◽

Vol 34 (3) ◽

pp. 607-616 ◽

Cited By ~ 21

Author(s):

C. DÍAZ-TIELAS ◽

E. GRAÑA ◽

M.J. REIGOSA ◽

A.M. SÁNCHEZ-MOREIRAS

Keyword(s):

Secondary Metabolites ◽

Broad Spectrum ◽

Biological Activities ◽

Crop Protection ◽

Plant Secondary Metabolites ◽

Naturally Occurring ◽

Molecular Events ◽

Novel Applications ◽

New Applications ◽

Synthetic Derivatives

ABSTRACT This review provides information on the biological activities of chalcones (whether natural or synthetic derivatives) on different organisms, as well as an overview of the functions and possible new applications of these plant secondary metabolites on crop protection, as eco-friendly pesticides and weed control agents. Naturally occurring chalcones have been used in traditional medicine for many years; however, recent scientific advances have shown that these molecules have a broad range of biological activities in a variety of organisms. A review on the major sources of chalcones and the main molecular events involved in the modes of action of these natural products is achieved. Chalcones are molecules with a broad spectrum of biological activities, which are of great interest in agriculture to control weeds and unwanted pests.

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An Updated Review on the Secondary Metabolites and Biological Activities of Aspergillus ruber and Aspergillus flavus and Exploring the Cytotoxic Potential of Their Isolated Compounds Using Virtual Screening

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2021/8860784 ◽

2021 ◽

Vol 2021 ◽

pp. 1-11

Author(s):

Fadia S. Youssef ◽

Abdel Nasser B. Singab

Keyword(s):

Secondary Metabolites ◽

Aspergillus Flavus ◽

Topoisomerase Ii ◽

High Resolution Mass Spectrometry ◽

Antioxidant Activities ◽

Biological Activities ◽

2D Nmr ◽

Aspergillus Species ◽

Cytotoxic Potential ◽

In Silico Studies

The secondary metabolites and biological activities of Aspergillus ruber and Aspergillus flavus were comprehensively reported. About 70 compounds were isolated from both species that belong to different classes using conventional and advanced chromatographic techniques and unambiguously elucidated employing one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) and high resolution mass spectrometry (HRMS). Some of them displayed promising antiviral, anti-inflammatory, and antioxidant activities. In silico studies were conducted on human cyclin-dependent kinase 2 (CDK-2), human DNA topoisomerase II (TOP-2), and matrix metalloprotinase 13 (MMP-13) in an effort to explore the cytotoxic potential of the diverse compounds obtained from both Aspergillus species. 1,6,8-Trihydroxy-4-benzoyloxy-3-methylanthraquinone (23) revealed the most firm fitting with the active pockets of CDK-2 and MMP-13; meanwhile, variecolorin H alkaloid (14) showed the highest fitting within TOP-2 with ∆G equals to −36.51 kcal/mole. Thus, fungal metabolites could offer new drug entities for combating cancer. Relevant data about both Aspergillus species up to August 2020 were gathered from various databases comprising Scifinder (https://scifinder.cas.org/scifinder/login) for secondary metabolite-related studies; meanwhile, for biology-related articles, data were collected from both PubMed (http://www.ncbi.nlm.nih.gov/pubmed/) and Web of Knowledge (http://www.webofknowledge.com) as well.

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Chemical diversity and bioactivity of marine sponges of the genus Oceanapia: A review

Mini-Reviews in Organic Chemistry ◽

10.2174/1570193x18666210225120944 ◽

2021 ◽

Vol 18 ◽

Author(s):

Keisham S. Singh ◽

Supriya Tilvi

Keyword(s):

Secondary Metabolites ◽

Pacific Coast ◽

Biological Activities ◽

Biological Properties ◽

Marine Sponges ◽

Chemical Diversity ◽

Rich Source ◽

Chemical Structures ◽

Anti Hiv ◽

Acetylenic Acids

: The marine sponges of the genus Oceanapia sp. is comprised of more than 50 species and are distributed in the seas around the tropical and subtropical regions. They are mainly found in the northern Indian oceans, Japan, and the south pacific coast. They are highly colored and known to be a rich source of various secondary metabolites, particularly, alkaloids. Several other secondary metabolites were also reported from this genus which include terpenes, sphingolipids, ceramides, cerebrosides, acetylenic acids, and thiocyanatins, etc. Many of these compounds isolated from this genus exhibited various biological properties including anticancer, antimicrobial, anti-HIV, ichthyotoxicity and nematocidal activities. Although several secondary metabolites have been reported from this genus, a dedicated review of the chemicals and biological activities of this genus is so far lacking. Keeping this in mind this review describes the various chemical entities isolated from the sponges of the genus Oceanapia detailing their chemical structures along with their reported biological properties.

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A reappraisal of fungi producing aflatoxins

World Mycotoxin Journal ◽

10.3920/wmj2008.1094 ◽

2009 ◽

Vol 2 (3) ◽

pp. 263-277 ◽

Cited By ~ 73

Author(s):

J. Varga ◽

J. Frisvad ◽

R. Samson

Keyword(s):

Secondary Metabolites ◽

Biosynthetic Pathway ◽

Aflatoxin Production ◽

Aspergillus Species ◽

Aflatoxin Biosynthesis ◽

Aspergillus Section Flavi ◽

Naturally Occurring ◽

Aflatoxin B ◽

Aspergillus Section

Aflatoxins are decaketide-derived secondary metabolites which are produced by a complex biosynthetic pathway. Aflatoxins are among the economically most important mycotoxins. Aflatoxin B1 exhibits hepatocarcinogenic and hepatotoxic properties, and is frequently referred to as the most potent naturally occurring carcinogen. Acute aflatoxicosis epidemics occur in several parts of Asia and Africa leading to the death of several hundred people. Aflatoxin production has incorrectly been claimed for a long list of Aspergillus species and also for species assigned to other fungal genera. Recent data indicate that aflatoxins are produced by 13 species assigned to three sections of the genus Aspergillus: section Flavi (A. flavus, A. pseudotamarii, A. parasiticus, A. nomius, A. bombycis, A. parvisclerotigenus, A. minisclerotigenes, A. arachidicola), section Nidulantes (Emericella astellata, E. venezuelensis, E. olivicola) and section Ochraceorosei (A. ochraceoroseus, A. rambellii). Several species claimed to produce aflatoxins have been synonymised with other aflatoxin producers, including A. toxicarius (=A. parasiticus), A. flavus var. columnaris (=A. flavus) or A. zhaoqingensis (=A. nomius). Compounds with related structures include sterigmatocystin, an intermediate of aflatoxin biosynthesis produced by several Aspergilli and species assigned to other genera, and dothistromin produced by a range of non-Aspergillus species. In this review, we wish to give an overview of aflatoxin production including the list of species incorrectly identified as aflatoxin producers, and provide short descriptions of the 'true' aflatoxin producing species.

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Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features

Molecules ◽

10.3390/molecules26247646 ◽

2021 ◽

Vol 26 (24) ◽

pp. 7646

Author(s):

Yhiya Amen ◽

Marwa Elsbaey ◽

Ahmed Othman ◽

Mahmoud Sallam ◽

Kuniyoshi Shimizu

Keyword(s):

Secondary Metabolites ◽

13C Nmr ◽

Biological Activities ◽

Biosynthetic Pathways ◽

Important Group ◽

Naturally Occurring ◽

Nmr Data ◽

Anti Inflammatory ◽

Drug Leads

Chromone glycosides comprise an important group of secondary metabolites. They are widely distributed in plants and, to a lesser extent, in fungi and bacteria. Significant biological activities, including antiviral, anti-inflammatory, antitumor, antimicrobial, etc., have been discovered for chromone glycosides, suggesting their potential as drug leads. This review compiles 192 naturally occurring chromone glycosides along with their sources, classification, biological activities, and spectroscopic features. Detailed biosynthetic pathways and chemotaxonomic studies are also described. Extensive spectroscopic features for this class of compounds have been thoroughly discussed, and detailed 13C-NMR data of compounds 1–192, have been added, except for those that have no reported 13C-NMR data.

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Recent Discovery of Heterocyclic Alkaloids from Marine-Derived Aspergillus Species

Marine Drugs ◽

10.3390/md18010054 ◽

2020 ◽

Vol 18 (1) ◽

pp. 54 ◽

Cited By ~ 3

Author(s):

Xu ◽

Yuan ◽

Li ◽

Keyword(s):

Secondary Metabolites ◽

Drug Development ◽

Marine Fungi ◽

Biological Activities ◽

Nitrogen Heterocycles ◽

Extreme Environments ◽

Structural Diversity ◽

Aspergillus Species ◽

Basic Nitrogen ◽

Future Drug

Nitrogen heterocycles have drawn considerable attention due to of their significant biological activities. The marine fungi residing in extreme environments are among the richest sources of these basic nitrogen-containing secondary metabolites. As one of the most well-known universal groups of filamentous fungi, marine-derived Aspergillus species produce a large number of structurally unique heterocyclic alkaloids. This review attempts to provide a comprehensive summary of the structural diversity and biological activities of heterocyclic alkaloids that are produced by marine-derived Aspergillus species. Herein, a total of 130 such structures that were reported from the beginning of 2014 through the end of 2018 are included, and 75 references are cited in this review, which will benefit future drug development and innovation.

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